Compound having oxadiazole ring structure substituted with pyridyl group, and organic electroluminescent device
a technology of pyridyl group and oxadiazole, which is applied in the direction of luminescent compositions, organic chemistry, thermoelectric devices, etc., can solve the problems of poor stability of pbd, insufficient electron mobility, and difficulty in achieving the effect of improving the emission efficiency and durability of conventional organic el devices
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example 1
(Synthesis of 1,3-bis[2-(2,2′-bipyridin-6-yl)-1,3,4-oxadiazol-5-yl]benzene (hereinafter referred to as BpyOXDm) (2))
[0079]0.63 g of 6-(2H-tetrazol-5-yl)-2,2′-bipyridine was dissolved in 10 ml of dehydrated pyridine, and 0.29 g of isophthaloyl dichloride was gradually added. Temperature was elevated to 115° C., and stirring was conducted for 6 hours under reflux. After cooling to room temperature, the reaction solution was poured into water, and a precipitated white solid was taken out by suction filtration, and washed with water. The solid obtained was vacuum dried at 80° C. for 20 hours, and purified with column chromatography (carrier: silica gel, eluting solution: chloroform / methanol=20 / 1) to obtain 0.62 g (yield 81%) of BpyOXDm. The product was identified with NMR analysis. The result of NMR analysis (CDCl3) was as follows. 9.071 ppm (1H), 8.639-8.714 ppm (6H), 8.325-8.477 ppm (4H), 8.037 ppm (2H), 7.756-7.854 ppm (3H), 7.330 ppm (2H).
example 2
(Synthesis of 1,4-bis[2-(2,2′-bipyridin-6-yl)-1,3,4-oxadiazol-5-yl]benzene (hereinafter referred to as BpyOXDp) (3))
[0080]0.67 g of 6-(2H-tetrazol-5-yl)-2,2′-bipyridine was dissolved in 10 ml of dehydrated pyridine, and 0.32 g of terephthaloyl dichloride was added. Temperature was elevated to 110° C., and stirring was conducted for 5 hours under reflux. After cooling to room temperature, the reaction solution was poured into water, and a precipitated white solid was taken out by suction filtration, and washed with water. The solid was vacuum dried at 80° C. for 20 hours to obtain a while crude product. By purifying with column chromatography, 0.58 g (yield 74%) of BpyOXDp was obtained. The product was identified with NMR analysis. The result of NMR analysis (CDCl3) was as follows. 8.736 ppm (2H), 8.640 ppm (4H), 8.463 ppm (3H), 8.260-8.384 ppm (4H), 8.060 ppm (2H), 7.932 ppm (2H), 7.380 ppm (1H).
example 3
(Synthesis of 2,6-bis[2-(2,2′-bipyridin-6-yl)-1,3,4-oxadiazol-5-yl]benzene (hereinafter referred to as BpyOXDPy) (4))
[0081]0.50 g of 6-(2H-tetrazol-5-yl)-2,2′-bipyridine was dissolved in 10 ml of dehydrated pyridine, and 0.26 g of 2,6-pyridinedicarbonyl dichloride was added. Temperature was elevated to 110° C., and stirring was conducted for 9 hours under reflux. After cooling to room temperature, the reaction solution was poured into water, and a precipitated white solid was taken out by suction filtration, and washed with water. The solid was vacuum dried at 80° C. for 20 hours to obtain a while crude product. By purifying with column chromatography, 0.12 g (yield 24%) of BpyOXDPy was obtained. The product was identified with NMR analysis. The result of NMR analysis (CDCl3) was as follows. 8.005-8.648 ppm (13H), 7.667 ppm (2H), 7.256 ppm (2H).
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